Relationship With Crossdressing - Office Family, Matter - Chapter 1

ALL STORY LIST | CHAPTERS - CH 2 | CH 3

Note: This is a completely separate story and not a continuation of 'Relationship With Crossdressing - Family Matter'. It follows a different plot, setting, and characters unrelated to the previous story.

The office buzzed with its usual Monday energy, keyboards clacking, coffee machines hissing, and the occasional burst of laughter from the break room. Tommy adjusted the hem of his fitted blazer, the soft fabric brushing against the lace-trimmed camisole underneath.

He’d taken bolder steps lately, swapping his usual slacks for an A-line skirt that swayed just above his knees. It felt right. Liberating. But the sideways glances from the accounting team told him not everyone agreed.

Karen’s office door swung open before he could sit down. “Tommy. Now.” Her voice was sharp, the kind of tone that made interns flinch. He followed her inside, the click of his low heels suddenly deafening in the silence.

She didn’t offer him a seat. “We’ve had complaints.” Karen tapped a manicured nail against a folder on her desk.

“The Henderson account said your ‘antics’ were unprofessional. They threatened to take their business elsewhere.”

Tommy’s stomach tightened. “Antics?”

“The” Karen gestured vaguely at him, her mouth twisting. “The getup. They called it a ‘sideshow.’”

Heat prickled up his neck. “I’m not in costume. This is how I dress.”

“And that’s your right,” Karen said, though her tone suggested otherwise. “But this is a workplace, not a runway. Tone it down.”

The argument with Lisa erupted that same night.

Tommy had just unclipped his earrings when the bedroom door slammed. Lisa stood there, her face pale, clutching his makeup bag, the one he kept hidden in his gym duffel.

“What the hell is this?” Her voice shook.

He reached for it, but she yanked it back. “Lisa, it’s just”

“Just what? Another secret? First it was the clothes, then the gym, now this?” She upended the bag, sending lipsticks and foundation bottles clattering across the dresser.

“Do you even know who you are anymore?”

The bathroom door down the hall creaked open. Emily eavesdropped. Tommy caught a glimpse of her wide eyes before she ducked back inside.

Lisa followed his gaze and lowered her voice to a furious whisper.

“She’s embarrassed, Tommy. The other moms talk. Her teacher asked if you were ‘going through something.’”

Tommy sank onto the bed. “I’m not transitioning. I’m not a woman. I just ” He struggled for the words. “I like how it feels. That’s all.”

Lisa’s laugh was brittle. “That’s all? You’re tearing this family apart for a feeling?”

The words hung between them, heavy and final. Somewhere down the hall, Emily’s door clicked shut.

The next morning, Tommy dressed carefully slacks, a button-down, no jewelry. The mirror reflected a stranger, but Karen would approve.

His phone buzzed as he left the house. A text from Rachel: Heard about Karen. HR at 3? I’ll go with you. Tommy hesitated, then typed back: Thanks. But I need to handle something at home first.

Lisa’s car was still in the driveway. She’d called in sick, or maybe she just couldn’t face him. He thought of Emily’s hollow stare at breakfast, the way she’d mumbled “Bye, Dad” without looking up.

The office elevator doors slid open. Karen nodded curtly as he passed her desk. Tone it down. For the first time, Tommy wondered if bending was the same as breaking.

The gym smelled of rubber mats and citrus-scented disinfectant, the usual soundtrack of clanging weights and low chatter filling the space. Tommy adjusted the straps of his sports bra beneath his fitted tank top, the fabric hugging his torso in a way that still felt thrillingly foreign. Mia had promised today’s session would focus on lower-body sculpting "for that feminine silhouette," she’d said with a wink.

He was mid-squat when he felt the weight of someone’s stare. Glancing sideways, he locked eyes with Derek from marketing, who was hovering by the dumbbell rack, his mouth slightly open. Tommy straightened, wiping sweat from his brow. Derek quickly looked away, but the damage was done. The air between them thickened with unspoken judgment.

Mia appeared at his side, her ponytail swinging. "Ignore him," she murmured, handing Tommy a resistance band. "He’s just mad his deadlift form is trash."

Tommy forced a laugh, but his stomach churned. He’d known this would happen eventually, someone from work seeing him here, dressed like this. The leggings, the bra, the way Mia had taught him to roll his hips when he walked to emphasize the curve of his waist. It was one thing to push boundaries at the office, another to exist like this in a space where muscles and testosterone usually ruled.

"You good?" Mia asked, nudging him.

"Yeah," Tommy lied, looping the band around his thighs. "Just wondering if I should’ve gone with the black sports bra instead. This pink one feels loud."

Mia rolled her eyes. "Please. You look hot. Own it." He tried. But as he moved through the exercises, hip thrusts, glute kickbacks, lateral lunges, he caught Derek whispering to another guy near the water fountain. Their laughter was sharp, pointed.

Rachel was waiting at their usual café after his shower, her eyebrows shooting up when she saw his face.

Tommy slumped into the chair, stirring his iced coffee listlessly. "Derek saw me at the gym. In outfit mode." Rachel’s lips pursed. "Let me guess. He’s being a little bitch about it?"

"Not to my face. But the office gossip mill’s gonna have a field day." He dragged a hand through his damp hair. "I just, I don’t get why it’s such a big deal. I’m not hurting anyone."

Rachel leaned forward. "Because it scares them. You’re not playing by the rules, and that makes people like Derek realize the rules are bullshit." She tapped her nails against the table.

"You know what you need? A statement piece. Something so undeniably you that they’ll either shut up or get used to it."

Tommy snorted. "Like what? A ball gown at the quarterly meeting?"

"Better." Rachel grinned. HR’s diversity training is next week. Walk in there like you own the damn room."

Lisa still wasn’t speaking to him. Tommy stood in the doorway of Emily’s bedroom, watching his daughter scroll through her phone, her face blank. "You need help with your history project?" he tried.

Emily didn’t look up. "I’m good."

The dismissal stung. He hovered, searching for words. "Em, about what your mom said"

"Dad." She finally met his eyes, her voice quiet. "I don’t care if you wear skirts or whatever. But everyone’s talking. Sarah K. said her mom called you a freak." Her throat bobbed. "I punched her."

Tommy’s breath caught. "You what?"

Emily shrugged, but her knuckles were faintly pink. "She deserved it." For the first time in days, something warm flickered in his chest. He wanted to hug her, but the space between them felt fragile. Instead, he nodded. "Thanks, kiddo."

Downstairs, Lisa was chopping vegetables with more force than necessary. Tommy hesitated, then grabbed his gym bag. "I’ll be back late," he said to the silence.

The gym was nearly empty at this hour. Mia had already left, but Tommy swiped in anyway, heading straight for the mirrors in the stretching area. He faced his reflection, the slight curve of his waist from weeks of targeted workouts, the way his posture had shifted, softer but still strong.

He pulled the hair tie from his wrist and gathered his hair into a messy bun. Then, slowly, he rolled his shoulders back and let his hips sway as he walked the length of the room.

No one was watching. No one was laughing. For now, that was enough.

The HR office smelled like stale coffee and industrial carpet cleaner. Tommy sat stiffly in a plastic chair, his knee bouncing under the table as Rachel scribbled notes beside him. Across from them, Sandra from HR, her blazer buttoned tight, her expression carefully neutral, flipped through the complaint Tommy had filed.

"So," Sandra said finally, setting the papers down. "You're alleging that Karen's comments about your attire constitute gender-based discrimination."

Tommy swallowed. "She told me to 'tone it down' after clients complained. But the dress code policy doesn't specify gendered clothing. Just 'professional attire.'"

Sandra's pen tapped against her notepad. "And you believe your choices fit that description?"

Rachel cut in before Tommy could answer. "A skirt and blazer aren't inherently unprofessional. If a woman wore this exact outfit, no one would blink." She slid a photo across the table, Tommy in the outfit from last week, polished and put-together.

Sandra's mouth tightened. "It's not that simple. Client perception "

"Is not an excuse for bias," Rachel said flatly.

Tommy's phone buzzed in his pocket. A text from Lisa: Emily’s teacher called. Again. His stomach knotted, but he forced himself to focus. "I just want to be judged on my work, not my clothes."

Sandra sighed. "I'll review the policy with leadership. But these things take time."

Time. The word settled like a weight. How much more time would he have to spend pretending?

Lisa was waiting at the kitchen table when he got home, her arms crossed. "Mrs. Keene said Emily disrupted class defending you. Again." Tommy dropped his bag. "What happened?"

"Some boy called you a" Lisa's voice cracked. "A slur. Emily threw a textbook at him."

The image hit Tommy like a punch, his daughter, small and furious, standing up for him when he wasn't there to do it himself. "Is she okay?"

"Detention for a week." Lisa rubbed her temples. "She shouldn't have to deal with this, Tommy. We shouldn't."

He reached for her hand, but she pulled away. "I'm trying to fix it," he said quietly.

"By doing what? Making it worse?" Lisa's eyes glistened. "Every time you push, the world pushes back harder. And it's not just you getting hurt."

Upstairs, Emily's door was shut, music blaring, angry bass throbbing through the floor. Tommy pressed his palm against the wood, but didn't knock. Some battles couldn't be won with words.

The next morning, Derek's voice carried across the office kitchenette. "dude's got a death wish. HR won't do shit." Tommy froze in the doorway, gripping his coffee mug.

Derek's buddy snorted. "Bet Karen fires him before the quarter's up. No way they let him keep prancing around." The mug shattered in the sink.

Both men spun around. Tommy didn't move, didn't speak, just stared until Derek paled and muttered, "Let's go."

Rachel found him minutes later, picking ceramic shards from the drain. "Well," she said, handing him a napkin, "if you wanted to make an impression."

Tommy's laugh was hollow. "I'm tired, Rach."

She squeezed his shoulder. "Then let's fight smarter." That afternoon, Karen called him into her office again. This time, a man in a crisp suit sat beside her corporate HR.

"Tommy," Karen began, her smile strained, "we value your contributions. But given the distractions lately, we think it's best if you transition off the Henderson account."

The man nodded. "A temporary reassignment. For team cohesion."

Tommy's pulse roared in his ears. This wasn't a compromise it was a demotion. He looked at Karen. "Is this because of the complaint?"

Her gaze flicked to the HR rep. "Of course not. It's business." The lie hung in the air between them, thick and sour. Tommy stood slowly. "I'll think about it."

He walked out before they could respond, Rachel falling into step beside him. "They're scared," she murmured.

Tommy glanced at the cubicles around them, curious eyes, whispered conversations. "Good."

For the first time, he didn't lower his voice. Let them listen. Let them hear. The game wasn't over yet.

The therapist's office was too warm, the kind of heat that made Tommy's blouse stick to the small of his back. He crossed his legs at the knee, the fabric of his pencil skirt pulling taut, and glanced at Lisa beside him, her hands clenched in her lap, her jaw set. Emily slouched in the chair between them, picking at her chipped nail polish like she wished she were anywhere else.

Dr. Alvarez leaned forward, her voice calm. "Lisa, you said on the phone you felt blindsided. Can you tell us more about that?"

Lisa exhaled sharply. "It's not about the clothes. It's about the lies. Hiding makeup, sneaking around like he didn't trust me enough to say anything."

Tommy winced. "I did try to talk about it. You said it was just a phase."

"That was two years ago!" Lisa's voice cracked. "You dropped it, so I thought"

"I didn't drop it. I just stopped bringing it up." Tommy twisted the ring on his finger, his wedding band, still there. "Every time I did, you looked at me like I'd asked you to set yourself on fire."

Emily made a small, wounded noise. Both of them turned to her.

"Em?" Tommy reached for her hand.

She yanked away. "Stop talking about me like I'm not here!" Her eyes were red-rimmed, furious. "You're both so busy being mad, you don't even see how humiliating this is for me!"

The room went still.

Dr. Alvarez spoke first. "Emily, what would make this easier for you?"

"I don't know!" Emily swiped at her cheeks. "Just stop pretending it's normal. No one else's dad dresses like." She gestured wildly at Tommy's outfit. "Like that!"

Tommy's throat tightened. "I know it's not normal. But it's me." Lisa made a small, broken sound. "Who even is that, Tommy? The man I married hated shopping. Now you spend more time on your hair than I do."

"Maybe I just never got to try before!" The words burst out of him, raw and unfiltered. "I spent thirty years playing a part because that's what everyone wanted. Now I'm figuring out what I want, and yeah, sometimes that's mascara! Sometimes it's skirts! That doesn't mean I'm a different person!"

Silence. Emily sniffled. "Do you want to be a woman?"

Tommy's anger deflated. "No, kiddo. I like being your dad. I just also like." He plucked at his blouse.

Lisa stared at him, really looked at him, for the first time in weeks. "You're sure?"

"Yeah." He managed a shaky smile. "Turns out I can be great at softball and great at color-matching foundation."

Emily let out a wet giggle. Just a tiny one, but it was enough.

Dr. Alvarez smiled. "Progress."

Dinner that night was tense but civil. Tommy cooked stir-fry, his one reliable dish, while Lisa set the table without speaking. Emily scrolled on her phone, but when Tommy served her plate, she muttered, "Thanks."

Later, as Tommy washed dishes, Lisa appeared beside him, drying a bowl with methodical precision. "I looked up some stuff," she said finally. "About gender non-conformity."

Tommy's hands stilled in the soapy water. "Yeah?"

"It said, It's not always about being trans." She hesitated. "That some people just like mixing things up."

"Yeah." He rinsed a plate, heart pounding. "Like me."

Lisa nodded, staring at the towel in her hands. "I still don't get it. But, I don't have to, do I?"

Tommy turned to her, soap suds dripping from his fingers. "No. You just have to believe me when I say I'm still me."

For the first time in weeks, she met his eyes and didn't look away.

The next morning, Tommy dressed carefully: slim-fit trousers, a lavender blouse, subtle pearl studs in his ears. No skirt today, not for this.

Emily paused in the hallway, backpack slung over one shoulder. Her eyes flicked over his outfit. "You look okay," she muttered.

Tommy grinned. "High praise." She rolled her eyes, but didn't argue. At the office, Karen avoided his gaze, but Rachel practically bounced over. "You're glowing. What happened?"

Tommy glanced at his phone, a text from Lisa: Pizza tonight? Your choice of toppings.

He smiled. "Family stuff."

Rachel raised an eyebrow. "Good family stuff?"

"Yeah." He straightened his blouse, feeling lighter than he had in months. "Really good."

The email from HR arrived at 9:03 AM a terse, corporate-speak response to Tommy’s complaint, stating that after "careful consideration," the company had determined Karen’s actions fell within "managerial discretion."

No policy changes. No apology. Just a single, patronizing line at the bottom: We encourage all employees to express themselves within professional boundaries.

Rachel read it over Tommy’s shoulder and let out a low whistle. "Wow. They really just said ‘deal with it’ in fifty fancy words."

Tommy’s fingers tightened around his coffee cup. He’d known this was likely, but the dismissal still stung. Across the office, Derek smirked at his desk, already whispering to a coworker.

Then Rachel’s eyes lit up.

"Oh no," Tommy said. "I know that look."

She grinned, pulling out her phone. "Remember when I said we should fight smarter?"

By lunchtime, the plan was in motion. Rachel had a group chat with half the office, mostly younger employees, plus a few sympathetic veterans who’d had their own run-ins with Karen. The message was simple:

Express yourself within professional boundaries. Tomorrow. Be creative.

Tommy hesitated before hitting send on his own contribution, a photo of his favorite outfit, the one Karen had called "distracting": a navy blazer, a cream silk blouse, and a knee-length pencil skirt. Wear what they can’t ignore, he typed.

The replies came fast. I’ve got a floral tie that’ll piss Derek off just by existing. My nonbinary ass is breaking out the binder AND a skirt. Let’s confuse everybody.

Karen’s gonna have an aneurysm when she sees my crop top under this blazer. Tommy laughed, the tension in his chest loosening for the first time all week.

That evening, Lisa caught him digging through his closet, pulling out his boldest pieces: a crimson blouse with ruffled sleeves, a charcoal pinstripe skirt he’d never dared to wear to work.

"Big day tomorrow?" she asked, leaning against the doorframe.

Tommy hesitated. Lisa had been trying, but this an organized rebellion against his boss wasn’t exactly a casual conversation topic. "Kind of, we’re making a statement at work."

Lisa raised an eyebrow. "What kind of statement?"

"That I’m not the only one who thinks the dress code is bullshit."

To his surprise, Lisa snorted. "About time." She reached past him, plucking a teal scarf from the shelf. "Wear this. It’ll make your eyes pop."

Tommy blinked. "You’re not mad?"

Lisa sighed. "I’m still adjusting. But I’m not gonna let some uptight boss bully you." She flicked the scarf at him. "Just don’t get fired, okay?" The next morning, the office was a riot of color and defiance.

Rachel strutted in wearing a tailored three-piece suit with six-inch stilettos. Jamal from IT had swapped his usual polos for a sleeveless mesh top under his work badge lanyard. Even quiet, middle-aged Marcy from accounting showed up in a pantsuit so aggressively neon pink it hurt to look at.

Karen’s face when she walked in was worth every second of anxiety.

"What the hell is this?" she hissed, grabbing Tommy’s arm.

He gently pulled free. "Professional self-expression. Like HR said."

Around them, the office buzzed, laughter, compliments, the click of phone cameras as people snapped photos for social media. Someone had already started a hashtag: #Express Yourself At Work.

By noon, corporate HR was blowing up Karen’s phone. By three, the local news had picked up the story.

And by five, as Tommy packed up his bag, Karen stormed out of an emergency leadership meeting, face flushed, voice shaking, and announced a "revised dress code policy" would be circulated next week.

Rachel high-fived Tommy so hard his palm stung.

"Told you," she whispered. "Sometimes you’ve gotta burn it down to build something better."

Tommy looked around at his coworkers at his people, all grinning in their glorious, unapologetic defiance, and realized, for the first time, he wasn’t fighting alone.

That night, Emily texted him a link to a TikTok video someone from the office had posted, footage of the rebellion, set to an empowerment anthem. The caption read: When your workplace tries to police gender, sometimes the whole squad shows up in skirts.

Emily’s message followed: Mom says you’re a bad influence. Also, can I borrow your red scarf?

Tommy laughed so hard he cried.